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10 Recent Trades MLB Teams Already Regret (And 10 Smart Deals)

One of the best times in sports is upon us. For the rest of September, teams will battle it out to get into the postseason and then duke it out in the playoffs to reach the Fall Classic. In less than a month’s time, fans will know which team is in the playoffs and which teams are going home.

When fans think about the playoffs, they think about all the moves and recent signings that have helped their teams get to October baseball. Some of these signings may not have seemed like a big deal but have paid dividends to the success of teams this season. Just think about the huge trade that brought Curt Schilling to the Diamondbacks, who would win the World Series that year. Or what about the St. Louis Cardinals trading for Larry Walker in 2004, making it to their first World Series since 1987. While some trades have propped up a lineup, strengthened a rotation or patched a bullpen, not all trades worked out so well.

Trades like Johnathan Papelbon to the Nationals induced only swings and misses between Papelbon and Bryce Harper in the dugout during their brawl. Other trades like the Blue Jays trading for R.A. Dickey, sending away Noah Syndergaard to the Mets, were laughably bad as well. These are just a few examples of trades that have been complete busts in the past, but even today with playoffs nearing, many teams are undoubtedly regretting certain trades, while other teams are looking like geniuses. This article is about some of these more recent trades. In this article, we look at 10 trades teams are already regretting, and 10 that were smart deals.

20 Regret: The Pirates Trading For Chris Archer

Charles LeClaire-USA TODAY Sports

Ouch does this trade sting. Not only did the Pirates fail to address their team’s needs (everything), but they got a less than advertised pitcher in Chris Archer. The former Tampa Bay Ray is sporting an ERA well above 5.00, a mediocre record and very few innings. Worse yet, Archer already found himself on the DL.

The Pirates needed a pitcher to fill Gerrett Cole’s cleats, but Chris Archer isn’t that guy.

Pittsburgh needs prospects to restart this team. Of course, the Pirates got some prospects that they hope will be ready by 2019, thy had to give some up to get a pitcher who is far from his former All-Star self.

19 Smart: The Astros Trading For Justin Verlander

Brad Rempel-USA TODAY Sports

Obviously, this trade worked out. When Astros fans began to panic after the trade deadline in 2017, Justin Verlander was sent to Houston mere seconds before the waiver trade deadline expired. The rest is history as Verlander won all of his regular season starts with Houston, won two games in the ALDS and went 2-0 with an ERA of 0.56 in the ALCS, making him the ALCS MVP.

Verlander is still pitching well for Houston with an ERA under 3.00, and with the Astros looking to repeat, his career postseason ERA just above 3.00 looks pretty promising. Giving up prospects for a World Series ring and a strong possibility for another is a small price to pay for Verlander’s arm.

18 Regret: The Dodgers Trading For Manny Machado

Gary A. Vasquez-USA TODAY Sports

L.A. may not completely regret acquiring Manny Machado yet, but anything short of a World Series will make this trade look like an epic failure. With the Dodgers giving up some excellent prospects, and Kershaw not getting any younger, L.A. is all-in to win the World Series this year. Unfortunately, that’s not a sure thing as many have predicted.

The National League is about as tight as it can be, and the Dodgers will be fortunate to make the playoffs at all to say nothing about the World Series. Their bullpen is a train wreck and their rotation hasn’t spread fear in the eyes of batters either. Meanwhile, Mannywood 2.0 is posting one of his lowest SLG and OPS percentages of his career since coming to L.A. That could change quickly, but it still might not be enough.

17 Smart: The Cubs Trading For Cole Hamels

Patrick Gorski-USA TODAY Sports

Yu Darvish and the Cubs were taking a lot of heat for Yu’s lackluster 2018 performance and rightfully so. Darvish has been terrible and worse yet, he’s done for the season. Cubs’ President of Baseball Operations, Theo Epstein has to be regretting that signing and knew he needed a strong replacement arm in the rotation if he wanted to compete. As a result, Epstein made the trade to make Cole Hamels a Cub.

The Cubs lost a couple good minor leaguers, but this Cubs team doesn’t just want one ring.

They addressed their starting pitcher need and gambled on Cole Hamels being the Hamels of old. The gamble has paid off so far, as Hamels has been lights out, and now the Cubbies have a playoff pitcher that looks far more formidable than Darvish.

16 Regret: The Red Sox Trading For Ian Kinsler

Paul Rutherford-USA TODAY Sports

This trade may look okay only because the Red Sox were getting nothing at second base. With Dustin Pedroia looking done for the season, Ian Kinsler was traded to the Red Sox to fill that void. Unfortunately, Ian Kinsler isn’t exactly tearing it up in Boston either.

The Red Sox were winning just fine without second base help, but one has to wonder if Boston could have waited for Daniel Murphy to become available before signing Kinsler, who is posting career low numbers. The Red Sox will go far in the postseason even with Kinsler’s power numbers down, but adding Daniel Murphy to the club instead of Kinsler would have secured another ring without question.

15 Smart: The Yankees Trading For J.A. Happ

Noah K. Murray-USA TODAY Sports

Like the Cubs, the Yankees filled a huge need in the starting rotation and signed J.A. Happ from Toronto. Happ was pitching well for the lowly Blue Jays with a 10-6 record and has since won four straight with New York. The best part is the Yankees didn’t even have to sell the farm to bring Happ in.

With Happ, Luis Severino won’t have to carry the rotation on his own, and even better, Happ has a career ERA under 3.00 against the team the Yankees are chasing, the Boston Red Sox. Happ solidifies the Yankees starting rotation, and with their potent lineup, the Yankees will be very dangerous even as a Wild Card team.

14 Regret: The Dodgers Trading For John Axford

Dennis Wierzbicki-USA TODAY Sports

The Dodgers are trying to get back to the World Series, but their pitching just won’t allow it. Their bullpen has been absolutely miserable and in mid-August, posted an ERA of nearly 5.00. Because of bullpen meltdowns, the Dodgers have scraped the bottom of the barrel and signed John Axford in an effort to patch up some holes.

Sadly, Axford hasn’t been the answer to the surprise of no one.

Axford, in just over three innings pitched, has been punished for six runs, posting an ERA above 16.00. Worse yet, Axford has shelved himself on the DL already. L.A. needs to get their bullpen under control or the golf clubs will be coming out a lot sooner than predicted.

13 Smart: The Reds Trading For Matt Harvey

Aaron Doster-USA TODAY Sports

Not only was “The Dark Knight” looking very human in his 2017 and 2018 seasons with the Mets, he was out right terrible. Matt Harvey posted a 6.70 ERA in 2017 and dealt a 6.00 ERA in four starts with New York in 2018. Harvey was moved to the bullpen but didn’t fare much better there. After refusing to go to the minors, the Mets sent Harvey to the Reds instead.

This deal was good for the Mets as they got rid of an ineffective headache in Harvey and his 7.00 ERA, for catcher, Devin Mesoraco. However, the Reds have benefitted as well. Apparently getting out of New York has done Harvey some good as the Dark Knight has risen again. With the last place Reds, Matt Harvey has a winning record and his ERA is respectable again.

12 Regret: The Rays Trading For Tommy Pham

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We’ll never really know what really happened between Tommy Pham and the Cardinals. Pham had a breakout year with the Red Birds in 2017, but his struggles at the plate saw Pham take a stint to the minors. Pham was not happy about the demotion and decided to publicly rip his teammates. A rumor circulated that Pham was unhappy with Cardinals’ management, which Pham denies, but his poor play and attitude in 2018 earned him a one way ticket to Tampa Bay regardless.

While the Rays should be happy to have St. Louis’ top prospect, Pham was hitting only .248 with the Cards this season. Pham isn't doing much better in Tampa, taking a trip to the DL and hitting under .200 beforehand. For now, the Cardinals look great after a trade that looked quite lopsided on paper.

11 Smart: The Mariners Trading For Mike Leake

Bob DeChiara-USA TODAY Sports

The Seattle Mariners are having a surprising season. Not only are they winning, but they are hanging with the defending Champions, the Houston Astros. Even more surprising is that Seattle is on this run, not with the help of King Felix but, with Mike Leake instead.

Since being traded to the Mariners from the Cardinals in 2017, Leake has a winning record, an ERA under 4.00 and is posting one of his best WARs of his career.

Considering Seattle needed strong pitching and gave up almost nothing, the Mariners have to be loving this deal. Meanwhile, Leake is loving his new home, pitching better in Seattle than any other team in the majors.

10 Regret: The Astros Trading For Roberto Osuna

Troy Taormina-USA TODAY Sports

What needs does a team with the best ERA and ranking in the top five in the league for almost every offensive category require? More bullpen help of course. Even World Series caliber teams can use bullpen help, but the Astros made a very controversial move to acquire troubled relief pitcher Roberto Osuna.

Osuna is coming off of a 75-game suspension. His impending arrival to Houston didn’t sit well with Astros’ ace, Justin Verlander, an outspoken critic against actions like Osuna's. On the field, Osuna is pitching well for Houston, but his acquisition isn’t helping the mood in the clubhouse.

9 Smart: Cleveland Trading For Brad Hand

David Richard-USA TODAY Sports

When Cleveland went to the World Series in 2016, they did so riding on the backs of their bullpen. In 2018, Cleveland is hoping to do so again with Andrew Miller returning to form. However, closer Cody Allen is looking quite hittable this year. With Allen looking human, the Indians bolstered their bullpen with the strong addition of Brad Hand.

With Allen struggling, Hand was just the thing the Tribe needed. Hand has a microscopic ERA and already has a hand-full of saves with Cleveland. If Hand continues his success, he could be the anchor Cleveland needs to finish teams off and move forward in the playoffs.

8 Regret: The Brewers Trading For Jonathan Schoop

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No one should be surprised that the Brewers are doing well this year. They are a young, hungry team, and they are only going to get better. With the Brewers in the playoff hunt, Milwaukee got in on Baltimore’s yard sale and acquired Jonathan Schoop.

The problem is Schoop isn’t a major need for Milwaukee.

Their rotation right now isn’t good enough to win a ring, and Schoop won't push them past the NLDS, if they even get there. To hammer home that this deal stinks, Schoop is hitting around a whopping .200 since coming to Milwaukee. Worse yet, they had to get rid of young prospects which have been the building blocks that helped make the team who they are today.

7 Smart: The Phillies Trading For Asdrúbal Cabrera

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With the Mets and Nationals crumbling, the Braves and the Phillies have taken the reigns of the NL East. Philadelphia is a young club, but the National League is wide open for playoffs. Philly is hoping to squeak in by either winning their division or the wild card. Aaron Nola and Odubel Herrera are doing their part, but the Phillies needed help at shortstop. Thankfully, they got it in the form of Asdrúbal Cabrera.

The Mets found themselves sellers this season, and sent Cabrera to Philadelphia for minor leaguer, Franklyn Kilome. Cabrera has been in a slump for Philly, but was coming off of a .277 average with the Mets. Even in a slump, he’s still a major upgrade from Scott Kingery.

6 Regret: The Giants Trading For Evan Longoria

Sergio Estrada-USA TODAY Sports

The Giants are hovering around .500, but they are a ways away from competing in the potent NL West. Instead of making strange trades for Andrew McCutchen and Evan Longoria that haven’t moved the needle, San Francisco should have replenished their shallow farm system.

The Giants weren’t ready to compete this year and won’t be for a while with the Dodgers and Rockies playing good baseball right now. Yet, they refuse to admit this and rebuild. San Fran should be looking ahead rather than signing Longoria whose best days are likely behind him. Currently, “Longo” is posting his lowest OPS ever, didn’t come cheap and is currently stuck with the Giants for the next few seasons.

5 Smart: The Brewers Trading For Mike Moustakas

Richard Mackson-USA TODAY Sports

Unlike the Johnathan Schoop trade, the Brewers have no regrets trading for Mike Moustakas’ big bat. The Brewers are third in the National League and “Moose,” who cranked nearly 40 home runs in 2017, should help add to that.

Granted the ball hasn’t been flying off of Moustakas’ bat since joining the club, but the Brewers now have another dangerous batter for Milwaukee’s playoff hopeful lineup.

What sweetens the deal even further is that the Brewers got Moustakas for almost nothing. The deal shed Brett Phillips, who was giving Milwaukee nothing in the outfield, and Jorge Lopez, who now has a laughable ERA since leaving the Brew Crew.

4 Regret: The Braves Trading For Adam Duvall

Brett Davis-USA TODAY Sports

Most people had it wrong with the NL East, thinking the Nationals and Mets were going to run away with the division, but The Braves have replenished their farm system and are, not only major league ready but, playoff ready, well ahead of schedule. With the National League so tight, and Atlanta outperforming expectations, the Braves have found themselves as unforeseen buyers this season. That being said, the trade for Adam Duvall has to leave fans scratching their heads.

The Braves needed rotation help more than anything but instead got themselves a pinch hitter. Duvall has pop, but with the Braves, he’s hitting well below .200. Not that Duvall can’t provide a key hit, but right now, Duvall’s WAR being in the negative as a Brave just shows how crucial he really is to this team.

3 Smart: The Cardinals Trading For Chasen Shreve

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The Cardinals were looking dead in the water and riddled with injuries. Cardinals management made some changes, fired their manager and brought up some of their young arms from the minor leagues. Since then, the Cardinals have transformed into one of the most dangerous teams in the NL and solidified their shaky bullpen.

After removing some of the duds like Greg Holland, St. Louis replaced their bullpen with young arms and traded Luke Voit to the Yankees for Chasen Shreve. Shreve has helped strengthen their bullpen with an ERA under 3.00 and has helped turn the Cardinals’ weakness into one of their strengths.

2 Regret: The Mariners Trading For Zach Duke

Joe Nicholson-USA TODAY Sports

The Seattle Mariners are doing surprisingly well in the competitive AL West, and like most teams, Seattle has attempted to bolster their bullpen. Zach Duke pitched great out of the bullpen since being converted from a starter and pitched well in 2018 for the Minnesota Twins.

The Mariners were hoping to get more of the same, but unfortunately, the Mariners haven’t seen the Zach Duke they were hoping for.

Since coming to Seattle, Duke has an ERA over 8.00 and a WAR in the minus. Worse yet, the Mariners haven’t addressed their rotation. Unless Duke finds his bullpen magic, this trade looks like a bust.

1 Smart: The Phillies Trading For Wilson Ramos

Nick Turchiaro-USA TODAY Sports

The Philadelphia Phillies are young but make no mistake, they are a great team. With the playoffs within reach, the Phillies made a big trade for one of the best offense catchers in the league, Wilson Ramos.

Even though Jorge Alfaro was hitting well, “The Buffalo” is still an upgrade at catcher. Ramos was traded from the Tampa Bay Rays and was hitting nearly .300 with them. Now as a Philly, Ramos is hitting above .400. He’s only a rental, but he also won’t be holding down any of the young players in the farm system next year. With his big bat in the lineup this year, The Phillies have potential to go far in the playoffs.